Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 6| June 2010| Pages m629-m630
https://doi.org/10.1107/S1600536810016314

Penta­carbon­yl(imidazolidine-2-thione-κS)tungsten(0)

Salah Merniz,a Mahiedine Mokhtari,b Hénia Mousser,c* Lahcène Ouahabd and Abdelhamid Moussera

aDépartement de Chimie, Faculté des Sciences Exactes, Université Mentouri Constantine, Route de Ain El Bey, Constantine, Algeria, bDépartement de Chimie, Faculté des Sciences Exactes, Université Larbi Ben M'Hidi, Route de Constantine, Oum El Bouaghi, Algeria, cDépartement de Chimie Industrielle, Faculté des Sciences de l'Ingénieur, Université Mentouri Constantine, Campus Chaab Erssas, Constantine, Algeria, and dEquipe Organométallique et Matériaux Moléculaires, UMR6226 CNRS-Université de Rennes 1, Avenue du Général Leclerc, 35042, Rennes, France
*Correspondence e-mail: bouzidi_henia@yahoo.fr

(Received 6 April 2010; accepted 4 May 2010; online 8 May 2010)

In the title complex, [W(C3H6N2S)(CO)5], the W atom displays an octa­hedral coordination with five CO mol­ecules and an imidazolidine-2-thione mol­ecule. The W(CO)5 unit is coordinated by the cyclic thione ligand through a W—S dative bond. The W—S and C—S bond lengths are 2.599 (2) and 1.711 (9) Å, respectively. This last distance is significantly longer than that of free cyclic thio­ureas. The geometry of the title compound suggests sp3-hybridization of the S atom caused by the greatly polarized linkage W—S—C bond angle, which is close to tetra­hedral [109.50 (3)°]. In the crystal packing, N—H⋯O and N—H⋯S hydrogen-bonding inter­actions stabilize the structure and build up chains parallel to [101].

Related literature

For the properties of imidazolinethio­nes or cyclic thio­ureas, see: Gok & Çetinkaya (2004[Gok, Y. & Çetinkaya, E. (2004). Turk. J. Chem. 28, 157-162.]); Kuhn & Kratz (1993[Kuhn, N. & Kratz, T. (1993). Synthesis, pp. 561-562.]); Reglinski et al. (1999[Reglinski, J., Garner, M., Cassidy, I. D., Slavin, P. A., Spicer, M. D. & Armstrong, D. R. (1999). J. Chem. Soc. Dalton Trans. pp. 2119-2126.]); Crossley et al. (2006[Crossley, I. R., Hill, A. F., Humphrey, E. R. & Smith, M. K. (2006). Organometallics, 25, 2242-2247.]); Saito et al. (2007[Saito, K., Kawno, Y. & Shimoi, M. (2007). Eur. J. Inorg. Chem., pp. 3195-3200.]); Raper et al. (1983[Raper, E. S., Creighton, J. R., Oughtred, R. E. & Nowell, I. W. (1983). Acta Cryst. B39, 355-360.]). For hydrogen-bond motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Beheshti et al. (2007[Beheshti, A., Clegg, W., Dale, S. H., Hyvadi, R. & Hussaini, F. (2007). Dalton Trans. pp. 2949-2956.]). For related structures, see: Kuhn et al. (1998[Kuhn, N., Fahl, J., Fawzi, R. & Steimann, M. (1998). Z. Kristallogr. New Cryst. Struct. 213, 434.]); Mak et al. (1985)[Mak, T. C. W., Jasim, K. S. & Chieh, C. (1985). Inorg. Chim. Acta, 99, 31-35.]; Valdés-Martinez et al. (1988[Valdés-Martinez, J., Sierra-Romero, A., Alvarez-Toledano, C., Toscano, R. A. & García-Tapia, H. (1988). J. Organomet. Chem. 352, 321-326.], 1996[Valdés-Martinez, J., Enriquez, A., Cabrera, A. & Espinosa-Perez, G. (1996). Polyhedron, 15, 897-901.]); Pasynsky et al. (2007[Pasynsky, A.A., Il'in, A.N., Shapovalov, S.S., Torubayev, Yu.V. (2007). Russ. J. Inorg. Chem. 52, 875-878.]); Darensbourg et al. (1999[Darensbourg, D. J., Frost, B. J., Derecskei-Kovacs, A. & Reibenspies, J. H. (1999). Inorg. Chem. 38, 4715-4723.]).

[Scheme 1]

Experimental

Crystal data

  • [W(C3H6N2S)(CO)5]

  • Mr = 426.06

  • Triclinic, [P \overline 1]

  • a = 6.652 (1) Å

  • b = 7.8120 (12) Å

  • c = 11.6240 (15) Å

  • α = 84.071 (5)°

  • β = 85.042 (6)°

  • γ = 87.704 (7)°

  • V = 598.27 (15) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 9.84 mm−1

  • T = 293 K

  • 0.08 × 0.06 × 0.04 mm
Data collection

  • Bruker SMART 1K CCD area-detector diffractometer

  • Absorption correction: refined from ΔF (cubic fit to sinθ/λ, 24 parameters; Parkin et al., 1995[Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.]) Tmin = 0.526, Tmax = 0.867

  • 2623 measured reflections

  • 2623 independent reflections

  • 2324 reflections with I > 2σ(I)
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.106

  • S = 1.10

  • 2623 reflections

  • 154 parameters

  • H-atom parameters constrained

  • Δρmax = 1.44 e Å−3

  • Δρmin = −1.58 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O5i 0.86 2.39 3.039 (11) 133
N2—H2⋯S1ii 0.86 2.88 3.630 (9) 147
Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART. and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]) and ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]), PARST97 (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810016314/dn2555sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016314/dn2555Isup2.hkl

checkCIF report


Comment top

Imidazolinethiones or cyclic thioureas are an important classe of compounds with a wide variety of applications (Gok & çetinkaya, 2004; Kuhn & Kratz, 1993). The chemical interests of these cyclic thioureas lie in their face capping character, in their structural analogy with thiolated nucleosides and in their application to enzyme models (Reglinski et al., 1999; Crossley et al., 2006; Saito et al., 2007). The diverse properties of the cyclic thioureas have been attributed to the coordination ability of the heterocyclic RN—C(S)—NR' thioamide group, as a monodentate ligand, to both metallic and non-metallic elements, leading to stable electron donor–acceptor complexes (Raper et al., 1983). Our research has been focused for some time on coordination compounds of sulfur containing ligands with carbonyl metals. The structure of the Imidazolidine-2-Thione-W(CO)5 complex (I), was carried out and results are presented here.

The tungsten atom displays octahedral geometry with five CO and the Imidazolidine-2-Thione molecules (Fig. 1). The bond distances and angles in (I) are within normal range and are comparable to the corresponding values observed in similar structures (Saito et al., 2007; Mak et al., 1985; Valdés-Martinez et al., 1988; Valdés-Martinez et al., 1996; Pasynsky et al., 2007; Darensbourg et al., 1999). Such geometry of (I) suggests sp3 hybridization of the sulfur atom caused by the greatly polarized M—S—C linkage. Indeed, the W—S—C bond angles is 109.50 (3)° and is close to a tetrahedral angle. As expected, the C=S bond is elongated and the C(6)—S(1) interatomic distance is 1.711 (9) Å and it is significantly longer than that of free cyclic thiourea, 1.690 (2) Å (Mak et al., 1985; Kuhn et al., 1998). The bond length between the metal and trans-carbonyl carbon atoms is 1.970 (10) Å. This is substantially shorter than the metal cis carbonyl bonds. The average of the separations between the metal and cis carbonyls is 2.049 Å.

Intermolecular N—H···O hydrogen bonds generate R22(14) graph-set motif (Etter et al., 1990; Bernstein et al., 1995) resulting in the formation of a pseudo dimer. Further N-H···O [R22(14)] and N—H···S [R22(8)] interactions link these dimers forming chains parallel to the [1 0 1] direction (Table 1, Fig.2). The N-H···S hydrogen bond distance is in the same range of there observed in the heterocyclic thione complexes (Beheshti et al., 2007).

Related literature top

For the properties of imidazolinethiones or cyclic thioureas, see: Gok & Çetinkaya (2004); Kuhn & Kratz (1993); Reglinski et al. (1999); Crossley et al. (2006); Saito et al. (2007); Raper et al. (1983). For hydrogen-bond motifs, see: Etter et al. (1990); Bernstein et al. (1995); Beheshti et al. (2007). For related structures, see: Kuhn et al. (1998); Mak et al., 1985; Valdés-Martinez et al. (1988, 1996); Pasynsky et al. (2007); Darensbourg et al. (1999).

Experimental top

A solution of W(CO)6 (527 mg, 1.5 mmol) and Imidazolidine-2-thione (153 mg, 1.5 mmol) in 40 ml of dry THF was irradiated for 2 h with vigorous stirring. The excess of W(CO)6 was mouved by filtration and the solvent was evaporated under reduced pressure. The residue was recrystallised from THF/hexane (1:5 ratio). Bright yellow crystals were washed three times with portions of hexane, and dried under vacuum. Yield:(34%).

Refinement top

H atoms were positined geometrically, using a riding model with C—H = 0.96 Å (Uiso(H) = 1.5) (including free rotation about C—C and C—N bond) for methyl groups and with C—H = 0.93 and 0.97 Å (1.2 for aromatic and methylene groups) times Ueq(C).

Structure description top

Imidazolinethiones or cyclic thioureas are an important classe of compounds with a wide variety of applications (Gok & çetinkaya, 2004; Kuhn & Kratz, 1993). The chemical interests of these cyclic thioureas lie in their face capping character, in their structural analogy with thiolated nucleosides and in their application to enzyme models (Reglinski et al., 1999; Crossley et al., 2006; Saito et al., 2007). The diverse properties of the cyclic thioureas have been attributed to the coordination ability of the heterocyclic RN—C(S)—NR' thioamide group, as a monodentate ligand, to both metallic and non-metallic elements, leading to stable electron donor–acceptor complexes (Raper et al., 1983). Our research has been focused for some time on coordination compounds of sulfur containing ligands with carbonyl metals. The structure of the Imidazolidine-2-Thione-W(CO)5 complex (I), was carried out and results are presented here.

The tungsten atom displays octahedral geometry with five CO and the Imidazolidine-2-Thione molecules (Fig. 1). The bond distances and angles in (I) are within normal range and are comparable to the corresponding values observed in similar structures (Saito et al., 2007; Mak et al., 1985; Valdés-Martinez et al., 1988; Valdés-Martinez et al., 1996; Pasynsky et al., 2007; Darensbourg et al., 1999). Such geometry of (I) suggests sp3 hybridization of the sulfur atom caused by the greatly polarized M—S—C linkage. Indeed, the W—S—C bond angles is 109.50 (3)° and is close to a tetrahedral angle. As expected, the C=S bond is elongated and the C(6)—S(1) interatomic distance is 1.711 (9) Å and it is significantly longer than that of free cyclic thiourea, 1.690 (2) Å (Mak et al., 1985; Kuhn et al., 1998). The bond length between the metal and trans-carbonyl carbon atoms is 1.970 (10) Å. This is substantially shorter than the metal cis carbonyl bonds. The average of the separations between the metal and cis carbonyls is 2.049 Å.

Intermolecular N—H···O hydrogen bonds generate R22(14) graph-set motif (Etter et al., 1990; Bernstein et al., 1995) resulting in the formation of a pseudo dimer. Further N-H···O [R22(14)] and N—H···S [R22(8)] interactions link these dimers forming chains parallel to the [1 0 1] direction (Table 1, Fig.2). The N-H···S hydrogen bond distance is in the same range of there observed in the heterocyclic thione complexes (Beheshti et al., 2007).

For the properties of imidazolinethiones or cyclic thioureas, see: Gok & Çetinkaya (2004); Kuhn & Kratz (1993); Reglinski et al. (1999); Crossley et al. (2006); Saito et al. (2007); Raper et al. (1983). For hydrogen-bond motifs, see: Etter et al. (1990); Bernstein et al. (1995); Beheshti et al. (2007). For related structures, see: Kuhn et al. (1998); Mak et al., 1985; Valdés-Martinez et al. (1988, 1996); Pasynsky et al. (2007); Darensbourg et al. (1999).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST97 (Nardelli, 1995) and Mercury (Macrae et al., 2006).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Partial packing view of (I) showing the chain formed by N-H···O and N-H···S hydrogen bonds shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) -x, -y+1, -z+2; (ii) -x+1, -y+1, -z+1].
Pentacarbonyl(imidazolidine-2-thione)tungsten(0) top
Crystal data top
[W(C3H6N2S)(CO)5]Z = 2
Mr = 426.06F(000) = 396
Triclinic, P1Dx = 2.365 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.652 (1) ÅCell parameters from 9229 reflections
b = 7.8120 (12) Åθ = 1.0–27.1°
c = 11.6240 (15) ŵ = 9.84 mm−1
α = 84.071 (5)°T = 293 K
β = 85.042 (6)°Prism, yellow
γ = 87.704 (7)°0.08 × 0.06 × 0.04 mm
V = 598.27 (15) Å3
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		2623 independent reflections
Radiation source: fine-focus sealed tube2324 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
Detector resolution: 8.192 pixels mm-1θmax = 27.2°, θmin = 3.0°
ω scanh = −8→8
Absorption correction: part of the refinement model (ΔF)
(cubic fit to sinθ/λ, 24 parameters; Parkin et al., 1995)		k = −9→10
Tmin = 0.526, Tmax = 0.867l = 0→14
2623 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0555P)2 + 0.8559P]
where P = (Fo2 + 2Fc2)/3
2623 reflections(Δ/σ)max = 0.001
154 parametersΔρmax = 1.44 e Å−3
0 restraintsΔρmin = −1.58 e Å−3
Crystal data top
[W(C3H6N2S)(CO)5]γ = 87.704 (7)°
Mr = 426.06V = 598.27 (15) Å3
Triclinic, P1Z = 2
a = 6.652 (1) ÅMo Kα radiation
b = 7.8120 (12) ŵ = 9.84 mm−1
c = 11.6240 (15) ÅT = 293 K
α = 84.071 (5)°0.08 × 0.06 × 0.04 mm
β = 85.042 (6)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		2623 independent reflections
Absorption correction: part of the refinement model (ΔF)
(cubic fit to sinθ/λ, 24 parameters; Parkin et al., 1995)		2324 reflections with I > 2σ(I)
Tmin = 0.526, Tmax = 0.867Rint = 0.000
2623 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.106H-atom parameters constrained
S = 1.10Δρmax = 1.44 e Å−3
2623 reflectionsΔρmin = −1.58 e Å−3
154 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
W10.04631 (4)0.22504 (4)0.75225 (2)0.05469 (14)
S10.1747 (3)0.4882 (3)0.61423 (18)0.0631 (5)
O1−0.0857 (14)−0.1215 (10)0.8903 (7)0.093 (2)
O20.4366 (12)0.1909 (13)0.8942 (7)0.097 (2)
O3−0.3638 (10)0.2376 (10)0.6320 (6)0.0757 (17)
O40.2472 (17)0.0053 (12)0.5555 (8)0.106 (3)
O5−0.1845 (13)0.4202 (12)0.9529 (6)0.088 (2)
N10.3318 (15)0.6250 (13)0.7912 (7)0.088 (3)
H10.23600.58820.84090.106*
N20.5082 (13)0.6600 (11)0.6281 (7)0.075 (2)
H20.54340.65430.55560.090*
C1−0.0386 (15)0.0069 (13)0.8400 (8)0.071 (2)
C20.3013 (13)0.2079 (12)0.8406 (7)0.0634 (19)
C3−0.2170 (11)0.2399 (10)0.6719 (7)0.0533 (15)
C40.1775 (14)0.0833 (12)0.6262 (8)0.0626 (19)
C5−0.0988 (13)0.3583 (12)0.8803 (8)0.0624 (19)
C60.3454 (12)0.5942 (10)0.6806 (7)0.0587 (17)
C70.4921 (17)0.7255 (14)0.8196 (9)0.077 (2)
H30.56450.66600.88160.093*
H40.44200.83650.84220.093*
C80.6264 (17)0.7454 (15)0.7050 (9)0.079 (3)
H50.64470.86560.67730.094*
H60.75740.68840.71300.094*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
W10.0489 (2)0.0648 (2)0.0505 (2)−0.00673 (13)−0.00158 (12)−0.00630 (13)
S10.0636 (11)0.0727 (12)0.0541 (10)−0.0159 (9)−0.0067 (8)−0.0045 (9)
O10.103 (6)0.088 (5)0.085 (5)−0.032 (4)−0.016 (4)0.016 (4)
O20.069 (4)0.141 (7)0.085 (5)0.002 (4)−0.029 (4)−0.010 (5)
O30.057 (3)0.099 (5)0.074 (4)−0.006 (3)−0.011 (3)−0.012 (3)
O40.126 (7)0.106 (6)0.086 (5)0.018 (5)0.010 (5)−0.040 (5)
O50.089 (5)0.109 (5)0.066 (4)0.010 (4)0.010 (4)−0.033 (4)
N10.088 (6)0.119 (7)0.063 (4)−0.038 (5)0.005 (4)−0.024 (4)
N20.078 (5)0.090 (5)0.059 (4)−0.030 (4)0.002 (4)−0.009 (4)
C10.070 (5)0.080 (6)0.068 (5)−0.013 (4)−0.020 (4)−0.010 (4)
C20.057 (4)0.079 (5)0.054 (4)−0.006 (4)0.001 (3)−0.006 (4)
C30.042 (3)0.064 (4)0.055 (4)−0.006 (3)−0.004 (3)−0.007 (3)
C40.059 (4)0.070 (5)0.060 (4)−0.006 (4)−0.004 (4)−0.009 (4)
C50.054 (4)0.077 (5)0.057 (4)−0.012 (4)−0.012 (3)−0.001 (4)
C60.061 (4)0.059 (4)0.056 (4)−0.004 (3)−0.002 (3)−0.006 (3)
C70.080 (6)0.079 (6)0.078 (6)−0.008 (5)−0.012 (5)−0.022 (5)
C80.077 (6)0.085 (6)0.077 (6)−0.031 (5)−0.003 (5)−0.012 (5)
Geometric parameters (Å, º) top
W1—C11.970 (10)N1—C61.327 (11)
W1—C42.042 (9)N1—C71.430 (13)
W1—C32.049 (7)N1—H10.8598
W1—C22.050 (9)N2—C61.294 (11)
W1—C52.055 (10)N2—C81.465 (12)
W1—S12.599 (2)N2—H20.8601
S1—C61.711 (9)C7—C81.536 (17)
O1—C11.148 (11)C7—H30.9700
O2—C21.134 (12)C7—H40.9700
O3—C31.118 (10)C8—H50.9700
O4—C41.130 (12)C8—H60.9700
O5—C51.118 (12)
C1—W1—C487.8 (4)C8—N2—H2123.5
C1—W1—C389.7 (3)O1—C1—W1178.9 (10)
C4—W1—C389.5 (3)O2—C2—W1175.7 (9)
C1—W1—C288.5 (4)O3—C3—W1175.3 (8)
C4—W1—C292.6 (4)O4—C4—W1178.8 (9)
C3—W1—C2177.1 (3)O5—C5—W1175.0 (9)
C1—W1—C589.7 (4)N2—C6—N1109.4 (8)
C4—W1—C5176.8 (3)N2—C6—S1124.2 (7)
C3—W1—C588.5 (3)N1—C6—S1126.3 (7)
C2—W1—C589.3 (3)N1—C7—C8102.3 (8)
C1—W1—S1172.4 (3)N1—C7—H3111.3
C4—W1—S184.6 (3)C8—C7—H3111.3
C3—W1—S189.4 (2)N1—C7—H4111.3
C2—W1—S192.8 (3)C8—C7—H4111.3
C5—W1—S197.8 (3)H3—C7—H4109.2
C6—S1—W1109.5 (3)N2—C8—C7101.7 (8)
C6—N1—C7113.4 (8)N2—C8—H5111.4
C6—N1—H1123.3C7—C8—H5111.4
C7—N1—H1123.3N2—C8—H6111.4
C6—N2—C8113.0 (8)C7—C8—H6111.4
C6—N2—H2123.5H5—C8—H6109.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.862.393.039 (11)133
N2—H2···S1ii0.862.883.630 (9)147
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula[W(C3H6N2S)(CO)5]
Mr426.06
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)6.652 (1), 7.8120 (12), 11.6240 (15)
α, β, γ (°)84.071 (5), 85.042 (6), 87.704 (7)
V (Å3)598.27 (15)
Z2
Radiation typeMo Kα
µ (mm−1)9.84
Crystal size (mm)0.08 × 0.06 × 0.04
Data collection
DiffractometerBruker SMART 1K CCD area-detector
Absorption correctionPart of the refinement model (ΔF)
(cubic fit to sinθ/λ, 24 parameters; Parkin et al., 1995)
Tmin, Tmax0.526, 0.867
No. of measured, independent and
observed [I > 2σ(I)] reflections		2623, 2623, 2324
Rint0.000
(sin θ/λ)max (Å−1)0.643
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.106, 1.10
No. of reflections2623
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.44, −1.58

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999), PARST97 (Nardelli, 1995) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.862.393.039 (11)133.2
N2—H2···S1ii0.862.883.630 (9)146.6
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+1, −z+1.
 

Acknowledgements

The authors thank the Algerian Ministère de l'Enseignement Supérieur et de la Recherche Scientifique for financial support.

References

First citationAltomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350.  CrossRef Web of Science IUCr Journals Google Scholar
 First citationBeheshti, A., Clegg, W., Dale, S. H., Hyvadi, R. & Hussaini, F. (2007). Dalton Trans. pp. 2949–2956.  Web of Science CSD CrossRef Google Scholar
 First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2001). SMART. and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
 First citationCrossley, I. R., Hill, A. F., Humphrey, E. R. & Smith, M. K. (2006). Organometallics, 25, 2242–2247.  Web of Science CSD CrossRef CAS Google Scholar
 First citationDarensbourg, D. J., Frost, B. J., Derecskei-Kovacs, A. & Reibenspies, J. H. (1999). Inorg. Chem. 38, 4715–4723.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationEtter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationGok, Y. & Çetinkaya, E. (2004). Turk. J. Chem. 28, 157–162.  Google Scholar
 First citationKuhn, N., Fahl, J., Fawzi, R. & Steimann, M. (1998). Z. Kristallogr. New Cryst. Struct. 213, 434.  Google Scholar
 First citationKuhn, N. & Kratz, T. (1993). Synthesis, pp. 561–562.  CrossRef Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationMak, T. C. W., Jasim, K. S. & Chieh, C. (1985). Inorg. Chim. Acta, 99, 31–35.  CSD CrossRef CAS Web of Science Google Scholar
 First citationNardelli, M. (1995). J. Appl. Cryst. 28, 659.  CrossRef IUCr Journals Google Scholar
 First citationParkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53–56.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationPasynsky, A.A., Il'in, A.N., Shapovalov, S.S., Torubayev, Yu.V. (2007). Russ. J. Inorg. Chem. 52, 875–878.  Google Scholar
 First citationRaper, E. S., Creighton, J. R., Oughtred, R. E. & Nowell, I. W. (1983). Acta Cryst. B39, 355–360.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationReglinski, J., Garner, M., Cassidy, I. D., Slavin, P. A., Spicer, M. D. & Armstrong, D. R. (1999). J. Chem. Soc. Dalton Trans. pp. 2119–2126.  Web of Science CSD CrossRef Google Scholar
 First citationSaito, K., Kawno, Y. & Shimoi, M. (2007). Eur. J. Inorg. Chem., pp. 3195–3200.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationValdés-Martinez, J., Enriquez, A., Cabrera, A. & Espinosa-Perez, G. (1996). Polyhedron, 15, 897–901.  Google Scholar
 First citationValdés-Martinez, J., Sierra-Romero, A., Alvarez-Toledano, C., Toscano, R. A. & García-Tapia, H. (1988). J. Organomet. Chem. 352, 321–326.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 6| June 2010| Pages m629-m630
https://doi.org/10.1107/S1600536810016314
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS